Osprey condos
We found 490 condos — enter your dates for availability
Explore Osprey condo rentals
Villa in Osprey that sleeps the whole family
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Windsor Lodge Unit 15, studio, close to the beaches, pool access
Sleeps 2 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
3 Bedroom Penthouse with Stunning Sunset Views of Blackburn Bay!
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Windsor Lodge Unit 19, studio, 1BR/1BA, close to the Beaches, pool access
Sleeps 4 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
Windsor Lodge Unit 3, studio, close to the beaches, pool access
Sleeps 4 · 1 bedroom · 1 bathroom
8.88.8 out of 10
Excellentexcellent
3 reviews(3 reviews)
Enjoy your own 2bd/2ba Condo, Pool, Pickleball, Tennis, amazing sunsets!
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
Top rated condo and apartment rentals - Osprey
Short vacation
1010 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
The apartment is perfect for a vacation it has everything you would need.
Pauline B.
Stayed Jan 2025
Great Stay
1010 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
Erinn & Marlin were GREAT. Communication & flexibility were amazing. Guest suite was exactly as featured.They surprised us with alot of extras which were really appreciated. Location was perfect & local recommendations were really helpful. Tks again we'll see you in the future
Eric I.
Stayed Mar 2024
Great stay
1010 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
We had a wonderful vacation in Siesta Key it is our second time at the Surf Shack and our host Jim made us feel welcome. All you need is at the villa, close to the beach and village for great restaurants if you do not want to cook. We feel at home at the Surf Shack and will definitely return. Thanks Jim.
Denis S.
Stayed Nov 2019
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Frequently asked questions
Are there any apartment vacation rentals in Osprey?
Book one of our 490 vacation condo rentals in Osprey that let you live more like a local compared to a hotel. Osprey Village, Bay Acres and Rivendell are popular areas to stay in.
How much does it cost to stay in an apartment vacation rental in Osprey?
It's not just the apartment vacation rental itself that controls how much you'll need to pay. Things like festivals and local events can increase demand for properties and result in more expensive prices. First-time visitor to Osprey? Book a longer getaway and you may find some vacation condo rentals offering discounts. Simply decide when you want to travel and let Vrbo take care of the rest.
When is the best time to rent a vacation condo in Osprey?
January is when the majority of Vrbo guests book an apartment vacation rental in Osprey, which is located in Sarasota County. On average, the temperature ranges from 14ºC (57ºF) to 20ºC (68ºF) during this time of year.
Where can I rent an Osprey vacation apartment with great views?
Vrbo makes it simple to find the great views you're looking for in your accommodations. Just use the "Location" filter to narrow down the kind of area you prefer to be in, and the views you want to immerse yourself in, while searching vacation condo rentals in Osprey.
Does Osprey have any weekend apartment rentals?
When you're craving a spur-of-the-moment escape, check out our vacation condo rentals in Osprey that are ideal for a weekend getaway. Simply key in your chosen travel dates to see what's available. Can't find an apartment vacation rental that checks all your boxes? Stay flexible with your travel plans and try searching on other dates.
Can I book a luxury apartment in Osprey?
Our luxury apartment vacation rentals in Osprey are all about keeping you pampered and relaxed. They combine practical features like kitchens and separate bedrooms with premium perks such as state-of-the-art appliances, lavish interiors, pools and hot tubs. Want to hear the best bit? Vrbo's vacation condo rentals are private so you and your group can experience the opulence and unparalleled comfort all for yourselves.
What are the top things to do in Osprey?
From Siesta Key Beach to Venice Beach and Mote Marine Laboratory & Aquarium, you're not short of options in Osprey, especially if you're getting away with the fam. Book one of our apartment vacation rentals and you'll have the ideal base to discover these and other top sights in the area.
Why should I book my apartment vacation rental with Vrbo?
Booking your apartment vacation rental with Vrbo means you get the whole place to yourselves — your own private retreat, with no distractions or interruptions from other people. Also, our flexible payment and cancellation policies allow you to change your plans if you need to.